TRIPLET EMITTER HAVING CONDENSED FIVE-MEMBERED RINGS

• US 20090165846A1
• Filed: 09/07/2006
• Published: 07/02/2009
• Est. Priority Date: 09/07/2005
• Status: Active Grant

• Current Assignee: BASF AG (BASF SE), Universitaet Braunschweig
• Original Assignee: BASF SE, Universitaet Braunschweig
• Inventors: Kroener, Michael, Weinaug, Ute Jana, Ammermann, Sven, Johannes, Hans-Hermann, Kowalsky, Wolfgang
• Granted Patent: US 8,278,238 B2
• Time in Patent Office: Days
• US Class Current: 136/256
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/104 with other heteroatoms
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: Y10T 428/31678 Of metal

Abstract

The present invention relates to light emitting compounds, especially to triplett emitters suitable for electrooptical applications. Compounds according to the invention are organometallic complexes of a metal, preferably Ir, having a backbone of one five-membered ring that is linked to a five- or six-membered ring, by an intermediate six-membered ring. These compounds are suitable for adaptation to the emission of light in the UV to NIR range by adaptation of atoms or groups within at least one of the five-membered or six-membered ring structures.

Claims

1. :

A compound suitable for electrooptic devices, having a structure of general formula I

wherein

cycle B is a five-membered ring;

cycle A is a six-membered ring; and

cycle C is a six-membered or a five-membered ring;

X1 is selected from the group consisting of CR′ and

N;

X2 is selected from the group consisting of NR′

, O, S, Se, Te, CR′

R″ and

SiR′

R″

;

X3, X4 are independently selected from the group consisting of N, NR′

, S, O, CR′

, CR′

R″

, CR′

═

CR″

, N═

N, CR′

=N, N═

CR″

, SiR′

, SiR′

R″

, Se and Te;

R′ and

R″

are selected from the group consisting of A1, CN, NA1A2, OA1, SA1, F, Cl, Br, I, CNO, NCO, CA1O, and COOA1;

A1 and A2 are selected from the group consisting of any substituted (hetero)alkyl, (hetero)aryl, and H;

Met is selected from the group consisting of Ir, Pt, Ru, Re, Pd and Os;

n=1 to 3 and m=3−

n for Met=Ir, Os, Ru, and Re;

n=1 to 2 and m=2−

n for Met=Pt and Pd;

R1, R2 are independently selected from the group consisting of A1, CN, NA1A2, OA1, SA1, F, Cl, Br, I, CNO, NCO, CA1O, and COOA1; and

is a monoanionic saturating

2. :

The compound according to claim 1, wherein A1 and/or A2 are substituted with polymerizable groups selected from the group consisting of aldehyde, alcohol, cyanato, isocyanato, an at least mono-unsaturated olefinic group, vinyl, alkylidene, allyl, oxethane, acryl, amine, oxirane, carbonic acid and ester groups.

3. :

The compound according to claim 1, wherein the cyclic structures A, B and C form a condensed system.

4. :

The compound according to claim 1, wherein the structure is according to the following formula II;

wherein R1, R2, R3, R4 and R5 are independently selected from the group consisting of A1, CN, NA1A2, OA1, SA1, F, Cl, Br, I, CNO, NCO, CA1, and COOA1;

A1, A2 are selected from the group consisting of any substituted (hetero)alkyl, (hetero)aryl, and H.

5. :

The compound according to claim 1, wherein any of R1 to R5 are linked to each other, forming an anellated substituent to one or more of cyclic structures A, B and/or C.

6. :

The compound according to claim 1, wherein the cyclic structures A, B and C are substituted with charge transport moieties.

7. :

The compound according to claim 1, wherein

Z1 and Z2 represent atoms which are linked by a chemical bond or by an intermediary group that arranges one, two or three additional atoms between Z1 and Z2;

Z1 and Z2 are independently selected from the group consisting of methylene, substituted methylene, N, NR1, S, 0, Se, Te, CR1, SiR1, CR1R2, SiR1R2, CR2=CR3, N═

N, and CR1=N;

R1 to R3 are independently selected from the group consisting of A1, CN, NA1A2, OA1, SA1, F, Cl, Br, I, SO₂A1, CNO, NCO, CA1O, and COOA1; and

A1 and A2 are selected from the group consisting of any substituted (hetero)alkyl, (hetero)aryl, carrying a polymerizable group, and H.

8. :

The compound according to claim 1, wherein the mono-anionic saturating ligand

represents a moiety selected from the group consisting of substituents comprising acetylacetonate, 2-pyridylacetate, dipivaloylmethanate, 2-pyridylformiate, and 2-(4H-[1,2,4]triazol-3-yppyridine as a subunit.

9. :

The compound according to, claim 1, wherein (hetero)alkyl is selected from the group consisting of linear, branched or cyclic hydrocarbons having 1 to 18 carbon atoms- and (hetero)aryl is selected from the group consisting of mono-, bi- and polyunsaturated linear, branched or cyclic hydrocarbons having 1 to 18 carbon atoms.

10. :

The compound according to claim 1, wherein the polymerizable group is selected from the group consisting of aldehyde, alcohol, cyanato, isocyanato, an at least mono-unsaturated olefinic group, vinyl, alkylidene, allyl, oxethane, acryl, amine, oxirane, carbonic acid and ester groups.

11. :

The compound according to claim 10, wherein the polymerizable group is linked to a polymeric group, selected from the group consisting of polyalkylene groups, matrix groups, electron transporting groups and hole transporting groups.

12. :

An oligomer, dendrimer or polymer, comprising at least two compounds according to claim 1 as moieties.

13. :

A triplett emitter in electrooptic devices comprising at least one compound according to claim 1.

15. :

A process for producing the compound of claim 1, comprising synthesizing said compound in the presence of an intermediate jahalogeno-complex, wherein the halogen is chlorine or bromine.

16. :

A process for producing an electrooptic device, comprising applying the compound according to claim 1 to a substrate.

17. :

The process according to claim 16, wherein the compound applied by coating from solution or sputtering.

18. :

The process according to claim 17, wherein the coating is spray, spin, dip or knife coating or printing.

19. :

The process according to claim 16, wherein organic layers and a final contacting electrode of the device are formed under vacuum.

20. :

The process according to claim 19, wherein the vacuum process is a PVD (physical vapour deposition), CVD (chemical vapour deposition), or an OVPD (organic vapour phase deposition) process.

21. :

An electrooptical device comprising the compound according to claim 1.

22. :

The electrooptical device according to claim 21, wherein the electrooptical device is an OLED, OFET, laser or photovoltaic device.

14. (canceled)